Hydrochloric Acid → HCID 22727296, compound

HRID 2086274Notes

Reaction equation

HRID 2086274 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]2[CH:6]=[C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([NH:19][CH:20]4[CH2:25][CH2:24][N:23]([C:26]5[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=5)[CH2:22][CH2:21]4)[C:15](=[O:32])[CH2:14]3)(=[O:12])=[O:11])[CH2:8][O:9][C:4]=2[CH:3]=1.[OH-].[Na+].Cl.[C:38](OC(=O)C)(=[O:40])[CH3:39]>C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:34]=[CH:33][C:5]2[CH:6]=[C:7]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([N:19]([CH:20]4[CH2:25][CH2:24][N:23]([C:26]5[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=5)[CH2:22][CH2:21]4)[C:38](=[O:40])[CH3:39])[C:15](=[O:32])[CH2:14]3)(=[O:11])=[O:12])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 9957779HCID 9957779, compound

Product 1

HCID 22727296HCID 22727296, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (95 mg) in acetic anhydride (4 ml) was stirred at 80° C. for 10 hours. The reaction mixture was concentrated and the residue obtained was combined with a 1N aqueous solution of sodium hydroxide and extracted with dichloromethane. The organic phase was washed with aqueous sodium bicarbonate and brine, dried and concentrated to obtain N-[(7-chloro-2H-benzopyran-3-sulfonyl)-2-oxo-1-piperazinyl]-N-[1-(4-pyridyl)-4-piperidinyllacetamide. The resultant free form was dissolved in ethyl acetate, and combined with a solution of hydrochloric acid in ethyl acetate to form a precipitate, which was collected by filtration, washed with ethyl acetate, dried under reduced pressure to obtain the title compound (90 mg) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with aqueous sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated
  7. customto obtain N-[(7-chloro-2H-benzopyran-3-sulfonyl)-2-oxo-1-piperazinyl]-N-[1-(4-pyridyl)-4-piperidinyllacetamide
  8. customto form a precipitate, which
  9. filtrationwas collected by filtration
  10. washwashed with ethyl acetate
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-06a4b9edb41247f48c404e051adf4094
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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